Bovine Metabolome Database: Showing metabocard for 2-Aminobenzoic acid (BMDB0001123)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:41:22 UTC

Update Date

2020-05-21 16:28:50 UTC

BMDB ID

BMDB0001123

Secondary Accession Numbers

BMDB01123

Metabolite Identification

Common Name

2-Aminobenzoic acid

Description

2-Aminobenzoic acid, also known as 2-aminobenzoic acid or 2-aminobenzoic acid, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. 2-Aminobenzoic acid exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. 2-Aminobenzoic acid exists in all living species, ranging from bacteria to humans. 2-Aminobenzoic acid participates in a number of enzymatic reactions, within cattle. In particular, 2-Aminobenzoic acid and formic acid can be biosynthesized from formyl2-aminobenzoic acid; which is mediated by the enzyme kynurenine formamidase. In addition, 2-Aminobenzoic acid and L-alanine can be biosynthesized from L-kynurenine through the action of the enzyme kynureninase. In cattle, 2-aminobenzoic acid is involved in the metabolic pathway called the tryptophan metabolism pathway. 2-Aminobenzoic acid is a potentially toxic compound.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2-Aminobenzoesaeure	ChEBI
2-Carboxyaniline	ChEBI
O-Aminobenzoesaeure	ChEBI
O-Aminobenzoic acid	ChEBI
O-Carboxyaniline	ChEBI
Vitamin L1	ChEBI
Anthranilic acid	Kegg
2-Aminobenzoate	Kegg
O-Aminobenzoate	Generator
Anthranilate	Generator
Anthranilic acid, cadmium salt	HMDB
Anthranilic acid, calcium (2:1) salt	HMDB
Anthranilic acid, monolithium salt	HMDB
Sodium anthranilate	HMDB
Anthranilic acid, dihydrochloride	HMDB
Anthranilic acid, hydrochloride	HMDB
Anthranilic acid, monosodium salt	HMDB
1-Amino-2-carboxybenzene	HMDB
2-Amino-benzoate	HMDB
2-Amino-benzoic acid	HMDB
2-Aminophenylacetate	HMDB
2-Aminophenylacetic acid	HMDB
Anthranate	HMDB
Anthranic acid	HMDB
Anthranilic acid GR	HMDB
Carboxyaniline	HMDB
H-2-Abz-OH	HMDB
Kyselina anthranilova	HMDB
Kyselina O-aminobenzoova	HMDB
O-Amino-benzoate	HMDB
O-Amino-benzoic acid	HMDB
O-Anthranilate	HMDB
O-Anthranilic acid	HMDB
Ortho-amidobenzoate	HMDB
Ortho-amidobenzoic acid	HMDB
Ortho-aminobenzoate	HMDB
Ortho-aminobenzoic acid	HMDB
Vitamin L	HMDB

Chemical Formula

C₇H₇NO₂

Average Molecular Weight

137.136

Monoisotopic Molecular Weight

137.047678473

IUPAC Name

2-aminobenzoic acid

Traditional Name

2-aminobenzoic acid

CAS Registry Number

118-92-3

SMILES

NC1=CC=CC=C1C(O)=O

InChI Identifier

InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)

InChI Key

RWZYAGGXGHYGMB-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzoic acids

Alternative Parents

Substituents

Aminobenzoic acid
Benzoic acid
Benzoyl
Aniline or substituted anilines
Vinylogous amide
Amino acid or derivatives
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aminobenzoic acid (CHEBI:30754 )

Ontology

Status

Expected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	146.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.5 mg/mL	Not Available
LogP	1.21	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	0.78	ALOGPS
logP	1.45	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
pKa (Strongest Basic)	1.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.01 m³·mol⁻¹	ChemAxon
Polarizability	13.29 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-014i-1950000000-5595652a2e8f93679437	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014i-1960000000-889ed538406d5aa57a5d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00xr-9650000000-e0611721f0bf7b5bb2f8	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00r6-2910000000-0daf33fe6231b5e15b0e	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-3970000000-3351c7d8036c42c4cd41	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kf-9400000000-b65ee27505e8c4bcca28	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-0490000000-4165d1d7b8fff53889dd	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1950000000-5595652a2e8f93679437	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1960000000-889ed538406d5aa57a5d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-9650000000-e0611721f0bf7b5bb2f8	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00r6-2910000000-0daf33fe6231b5e15b0e	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-3970000000-3351c7d8036c42c4cd41	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kr-7900000000-a9c510a71b30a8fcc1b8	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-7900000000-cb7be965685a5ee30fbd	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-00kf-9400000000-395d42e11895b80f4e9c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-8c390367e035aea8527a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-899b596a227cd9a1769d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-3cc9be013399e30d7eae	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-655ef8fc722e0b1b6d14	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-4d0520217d12a10f9273	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-bab8539624c8af4e6434	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-f51f2db6bf1da2e26d20	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-86d698a8c81a3e765840	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0900000000-6df94712ad580bebfd21	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-9100000000-a1ce64280c2d7f3b85df	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9000000000-454f848122c778e951ad	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-7de473c1ca6bf702b2ac	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-94f19baa1ae36f43be60	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-2900000000-c2bbbe5e00434e635ad2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-4900000000-f8f84a5536375300afbd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00r6-9200000000-fccd86d3a0a4bfe2e5d7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-014i-9000000000-91ceb340e5cf91473cba	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-80972c552b97ae764bc4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-f494672ce9de4818b8c5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0006-9300000000-9bbb2f00817538e072d5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0900000000-e7e07e78dd5baa5c3f87	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-54a3d793d6fbf0220b47	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0umi-9200000000-bd780d6ca957af006488	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000f-9800000000-93111d593c96a3298a6c	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-014u-9600000000-5b8e271f29d04a87c89a	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Epidermis
Fibroblasts

Pathways

Name	SMPDB/Pathwhiz	KEGG
Tryptophan Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001123

DrugBank ID

DB04166

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30754

References

Synthesis Reference

Wang, Chengyin; Yang, Jisheng; Wang, Honghai. Production of o-aminobenzoic acid from by-product o-nitrobenzoic acid. Huaxue Shijie (1999), 40(5), 274-277.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Kynureninase

General function:: Not Available
Specific function:: Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3-hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3-hydroxyanthranilic acid (3-OHAA), respectively. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
Gene Name:: KYNU
Uniprot ID:: F1MCH2
Molecular weight:: 52186.0

Reactions

L-Kynurenine + Water → 2-Aminobenzoic acid + L-Alanine	details

Enzyme Details

2. Kynurenine formamidase

General function:: Not Available
Specific function:: Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites.
Gene Name:: AFMID
Uniprot ID:: E1BLL5
Molecular weight:: 35460.0

Reactions

Formylanthranilic acid + Water → 2-Aminobenzoic acid + Formic acid	details

Showing metabocard for 2-Aminobenzoic acid (BMDB0001123)

Structure for BMDB0001123 (2-Aminobenzoic acid)

Enzymes

Reactions

Reactions